It totally depends. A weakened structure can hold pressurization for a while, and then suddenly (and possibly catastrophically) fail.

A famous example of this is American Airlines flight 96 (1972): https://en.wikipedia.org/wiki/American_Airlines_Flight_96

One minor UX gotcha: the alarm for a pressurization problem on a 737 is not all that intuitive.

https://en.wikipedia.org/wiki/Helios_Airways_Flight_522

I'd rather not trust my life to "probably". If there was some damage to the hull or a cargo door that could lead to failure, it's under more stress and is more of a hazard as the altitude increases.

To take a structurally damaged plane to altitude with that argument (if it holds pressure, it probably won’t explode) is reckless folly.

"probably"